


Sweetest Boy

by Chicktar



Category: Supernatural
Genre: Alternate Universe- No Supernatural, Anal Fingering, Anal Sex, Blowjobs, Bottom Dean, Multi, Oral Sex, Plot just as a frame for the smut, Prostitution, Rimming, hooker Dean, lots of smut, not so much plot
Language: English
Status: In-Progress
Published: 2017-10-11
Updated: 2018-06-04
Packaged: 2019-01-16 06:22:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 6,391
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12337224
Author URL: https://archiveofourown.org/users/Chicktar/pseuds/Chicktar
Summary: Dean is an in-training prostitute in a sex club.  Castiel is his trainer.  In this AU, the sex trade is a legit business.  Dean is dedicated to his training and especially to pleasing Castiel.  Castiel is dedicated to Dean.WARNING:  This is not intended to be actual underage, but Dean does have a lot of innocence and some childlike qualities in this fic, so if that bothers you, please proceed cautiously or do not read at all.





	1. Chapter 1

Castiel’s thigh was warm and steady beneath Dean’s cheek, the denim just the right mix of soft and rough.  He loved feeling Castiel’s fingers idly threading through his hair as he talked on the phone.

“Yes, I got the all clear on all your tests, Mr. Henricksen.  It looks like we’re all set for this Saturday at 8:00 p.m.”  A pause as he listened to the man on the other end.  Then, “Yes, you will have a full hour and you’re Dean’s last appointment of the day, so if we both wish to extend that time we can agree then.”  A longer pause.  “I understand and Dean is prepared to accommodate your request.  As we have discussed previously, please keep in mind that Dean is still in training, so I will be present in the room at all times and while I will not touch you, I may touch or speak to Dean throughout.”  A brief pause, and then Castiel pulled his hand from Dean’s hair.  “Very well.  We will see you Saturday.”  He hung up and set the phone down.

“Well, Dean, we’re all set.  Are you excited for Saturday?”

Dean nuzzled his face into Castiel’s thigh and let out a soft hum.  He wasn’t sure.  He was excited.  And nervous.

Castiel’s hand came down to touch his cheek and lifted his chin so Castiel could see his face.  Castiel peered at him for a moment and then rolled his hair back and stood.  He stepped over to the couch, sat and patted his lap.  “Come here, Dean, I want to talk to you.”

Dean moved quickly and smoothly to straddle Castiel’s lap.  He had been such a good boy, being patient all day and now he hoped desperately that Castiel would let him come, or at least make Castiel come.  But he wasn’t going to ruin his chances by acting up now.  Although he felt an intense desire to grind himself up against Castiel’s hard cock, he held very still and stayed quiet and attentive.

“Dean,” Castiel began, “I asked you a question and I would very much like an answer.  Are you excited for Saturday.” 

Dean still wasn’t sure how to answer.  He was excited.  He wanted to feel exciting new things, feel the hands of new people touching his skin, try to make them feel good, maybe even earn their praise and high marks in his training.  But he was also nervous.  And a little scared.  Part of him wished it could always just be he and Castiel alone.  “Yes, sir,” he finally decided on, biting his lip after.

Castiel brought a finger to his lips and said, “Dean” in an admonishing tone.

Dean withdrew his teeth and quickly licked his lips.

“Good boy.  We want to keep those beautiful lips nice and soft, don’t we?  Now.  About Saturday.  You said yes, and I believe you, but I think there’s something more.  I would like you to tell me how you’re feeling.”

Dean considered carefully which words were the right ones.  “Tingly.  Excited.  Hopeful.  Worried.”  That was good.  That covered it.

Castiel smiled at him and his fingers brushed Dean’s cheek fondly.  Dean leaned into it.  “What are you worried about?”

“A little bit about the clients—if they’re—I don’t know—if I can’t get into it with them.  I don’t want to disappoint you.”

Castiel leaned forward and pressed a gentle kiss to Dean’s forehead.  “It’s perfectly normal to be a bit nervous about your first time with real clients.  It may be a difficult process.  You may not click well with every one of them.  That’s why you need training—why you need to learn how to find ways to get that chemistry working, or at least get yourself going and fool them into feeling the chemistry.  But Dean, all I want from you on Saturday is for you to try and use what we have learned and do your best.  I promise you that as long as you are trying your best for me, I will be proud and happy.”

Dean let out a small grin.

“So you will see three clients on Saturday.  You will have a break between each one so we can eat and relax and clean up.  Each session is one hour, but for this first portion of your with-client training we have requested each client tell us exactly what they want to happen, so I will brief you on each client beforehand.  I will be with you the entire time.  Only you will be serving the clients, but I will be there to keep you safe, to observe and for anything else I think you need.  Do you understand?”

“Yes, sir.”  Dean was still nervous, but he could handle it.  Nothing bad would happen with Castiel there—all he had to do was exactly what Cas had trained him to do.

“Good boy.”  Castiel ran his fingers through Dean’s hair, pushing it back out of his eyes and then cupping his palm around the back of Dean’s neck.  “I am going to be so proud seeing you give pleasure to your clients.  You are going to be so beautiful, Dean.”  He leaned in and kissed Dean on the lips, and Dean melted beneath his touch.

*             *             *

Friday had passed primarily in some unexpected pampering.  Castiel had taken Dean for a manicure and pedicure and waxing of his ass and balls.  Then they had discussed each of his Saturday clients individually and Dean was surprised by how simple the requests were.  The first client wanted a blowjob culminating in coming on Dean’s face.  The second client was a woman who wanted to rim and finger Dean.  Apparently it was something her husband wanted that made her nervous to try without some experience.  The third client wanted to fuck Dean doggy style.  All clients were long time clients who had at least a twelve month clean history, so they were allowed to share fluids without protection.  Dean was glad—he secretly hated condoms—flesh, even unfamiliar flesh was so much better.

“So Dean, remind me—what is your job?”

“I’m a bed partner, sir.”

“Yes, but what is your _task_?”

“Sir?”

“What does a bed partner do for his or her clients?”

“I provide company, sexual plea—”

“Yes yes, but when you do what you do, what is it that you are giving your clients?”

Dean stared at Cas.  He knew he didn’t mean “a blowjob” or “a fuck.”

Castiel leaned forward, resting his elbows on his knees, leaning very close to where Dean was kneeling in front of him.  “Now that you are seeing clients, Dean, before each session, I want you to try to think about what your client is looking for from you.  It will be easier someday when you have repeat clients and you know them very well.  Right now, you don’t know any of these clients yet, so you have limited information to go on, but let’s try it.  Tell me about your first client tomorrow.”

“My first client will be Andrew.  He’s a 44 year old man.  He has requested a blowjob.”

“Good.  What else?”

“He wants to come on my face.”

“Good.  Anything else?”

Dean thought.  “No.  He didn’t provide any other specific requirements for me or the blowjob.”  He hadn’t asked for Dean to be wearing anything specific or take any particular position.  Without such details, Dean had just pictured himself naked and on his knees before a standing, clothed man, but he shouldn’t assume, he realized now.  “And I don’t know anything else about his background.”

“Good.  Okay, so you have very limited information this time.  So what is the one specific request you do have?”

“That he wants to come on my face?”

“Yes.  Good, Dean.  So we have done that.  You have come on my face and I have come on yours many times.  Think about how that made you feel when we did it.”

Dean considered.  “When you come on my face, I guess it depends on what else we are doing, but sometimes I feel dirty and wanton, sort of.  Sometimes it’s more like I feel like a special doted on pet.”  He closed his eyes and thought about the other way around.  He could see himself at the end of an extremely hot training session with Cas when he’d been practicing spanking and they had ended the session with his trainer on his knees beneath Dean begging for Dean’s come.  “When I come on your face, it makes me feel…strong, like I’m invincible.”

“Yes, Dean.  Exactly.  So if your client wants to stand over you, hold his solid, rock hard cock in his hand and see you waiting beneath him, with your soft, pretty face and sweet, pouty lips, ready and needy for his load, and jerk his seed in huge white spurts all over you, marking up your gorgeous face, give me one word—your best guess of how he wants to feel in that moment.”

“Powerful.”  Dean said it immediately without thinking.

“Yes!”  Castiel’s hand reached out and stroked Dean’s face.  “That’s so good, Dean.  That would be my guess.  Now, because you know so little about your client, you don’t want to get too locked in to one way of thinking, so this is just an exercise to help you prepare and maybe be a little more ready to act in the moment.  If the client shows signs that contradict that, you have to be prepared to shift gears.  But you have made a good, educated guess about what your client wants you to give him.  So now you can imagine what you can do and say to make him feel powerful.  You should still act as you’ve been trained—it needs to be natural for you in the moment to be truly satisfying for your client.  But I think you will find this process is helpful for you.  Now, let’s talk about the second client.”

And they did.  Then they had dinner and watched some movies for the evening.  Castiel forbade Dean to initiate sex with him or to masturbate that evening or in the morning as he said the client’s would appreciate it more if he were aroused during their sessions.  So they went to bed with Dean’s cock half hard from the afternoon spent talking with Castiel about sex with no release.  And Dean lay awake for quite awhile nervous and thinking about everything Cas had said.  He felt prepared and confident and his nerves had faded almost entirely into a light background static.


	2. Chapter 2

**Summary for the Chapter:**

> Dean's first client.

Dean followed Castiel as he stepped up to the door.  Cas turned and faced Dean, wrapping one hand around Dean’s neck, a touch that always grounded Dean—made him feel connected and more in the moment.  “Are you ready?”

“Yes, sir,” Dean said.  He hoped he sounded confident.

“And your client is going to feel?”

“Powerful.”  Dean could hear the conviction in his own voice.  He was so ready to use what he had learned to make his client feel exactly what he had come here to feel.

“Good boy, Dean,” Castiel said, as his hand curled a little tighter around Dean’s neck and pulled him close to share their breath.  “I’m proud of you.”

Then he was releasing Dean and turning back to the door.  He strode in and Dean followed behind.

The room was a standard—this client had not sought a special playroom—it looked like warm, luxury version of a studio apartment.  A large bed dominated one end of the space and the other end held a living room style setup of couch, easy chairs and end tables.  A man in a slightly rumpled suit sat in one of the chairs and rose when Cas and Dean entered.  Castiel stepped forward, extending his hand.

“Welcome, sir.  I am Castiel, Dean’s mentor.  And this is Dean.”  Cas stepped slightly to the side and indicated Dean with a soft gesture.  Dean stepped up and smiled softly, going for an effect of shy friendliness.  The man, Andrew, gave him a small smile and let his gaze drift down over Dean’s body.  With Dean’s advice, Dean had gone with a simple set of military fatigues, one size too small, that hugged his body tightly.  His feet were bare and he loved the soft, read-to-be-taken look he always felt that gave him.  Dean thought Andrew was happy with what he saw.

Castiel cleared his throat and Andrew looked back to him.  “Before your time begins, I just want to reiterate the procedure for today.  I am here solely for training purposes.  Unless you break one of our rules or otherwise put Dean in danger, I will not interact with you directly in any way.  I may, if I deem it appropriate for Dean, touch or speak to or with Dean.  You have agreed not to interfere with this contact and we have agreed to endeavor not to allow it to diminish your enjoyment.  If Dean’s training does interfere with your satisfaction in your encounter today, you will be granted a free replacement session with another bed partner of your choosing.  Is this acceptable?”

“Yes.  I’m…it’s fine.”

Castiel smiled widely then and stepped back, nodding to Dean.  Dean stepped forward slowly, his eyes trained on Andrew’s.  He noted that as he stepped forward, Castiel stepped further back, eventually leaning casually against the wall behind Andrew and crossing his legs gently at the ankle.

“Andrew?” Dean said, his voice low, as he stopped just in front of Andrew, close enough the man could lean forward to kiss him if he desired.  They were of a similar height, and Dean could feel the man’s warm breath on his chin.

Andrew nodded.

Dean licked his lips.  Painfully slowly.  “May I...” He began, as he let his hand begin to reach forward toward the other man and paused, as if uncertain, though he was quickly becoming anything but uncertain.  Andrew wanted him.  Already.  Nearly desperately.  “…touch you?”

Andrew nodded again.  His eyes were trained on Dean’s lips.

Dean let his mouth drop open just the slightest bit and brought his hands up to brush up the man’s dress shirt and slide under the sides of his suit jacket.  He pushed the jacket up and back, sliding it over the man’s shoulders and letting it drop to the floor.  Andrew looked hungry as Dean’s hands slid back over his shoulders, squeezing over them and slowly sliding back to his chest.

“Wow,” Dean whispered softly, bringing his hands to fist around Andrew’s tie.  He let his own gaze drift down to Andrew’s lips, while he slid one hand down Andrew’s chest and over his stomach.  He stared at Andrew’s mouth as he licked his lips in slow motion again and his hand slid down to cup Andrew’s cock, which was already at least half-hard it seemed.  He let in a quick inhale of breath, like a gasp, and squeezed gently, as he raised his eyes to Andrew’s again.

“How do you want me?” Dean asked, letting breathiness infuse his voice, and massaging Andrew’s erection.

“Knees,” Andrew said, and Dean reacted immediately with a soft, “yesssss” muttered under his breath and a drop to his knees, letting go of Andrew’s tie and cock to bring both hands up simultaneously to begin working Andrew’s buckle.  Dean could free a belt and open a man’s pants quicker than he could for himself, but instead he let his hands fumble almost frantically so that Andrew reached forward and wrapped his own hands around Dean’s and stilled them.  Dean looked up at him, peeking out from under his eyelashes and seeing Andrew’s darkened lust-filled eyes looking down.  Dean felt a little thrill at having gotten this reaction so quickly without any of their skin even touching until now.  He hadn’t thought about how powerful it would make _him_ feel to try to make _his client_ feel that way.

Andrew held Dean’s hands still for a few moments, then released them and began sliding his belt through the buckle and tugging the pin free from its hole.  He was moving slowly and gazing down intently at Dean.  He was drawing it out.  Dean let his hands slid over Andrew’s thighs and rest there as he locked his gaze onto Andrew’s hands.  His view was blocked now and he couldn’t see Castiel, but he hoped Castiel could see them well and thought Dean was doing a good job.

Andrew pulled his belt free and slipped the button open.  As he slid the zipper down, Dean let one of his hands drift down to rub roughly at his own completely un-forced hard-on.  Fuck, but it was a turn-on getting this reaction from a stranger.  And it wouldn’t hurt for Andrew to know that Dean was riled up with real need from their interaction.  With his pants open, Andrew reached his hands around to slip his fingers inside the waist at both hips and then he paused, staring down at Dean.  Dean let his hands fly up to meet Andrew’s and open wide.  He let his mouth fall just a little further open and brought his tongue forward to rest over his bottom teeth, not hanging out, but visible—suggestive.

Andrew reached a hand out and wrapped it around Dean’s cheek, letting his thumb rest on Dean’s bottom lip.  Dean let his tongue gently slide across it until Andrew slipped it in and Dean could suck it hungrily.  Andrew’s mouth curved up.  “Do you like that, baby?”

“Mmm,” Dean hummed around Andrew’s thumb.

“Do you want something bigger to suck on?”

“Mmmph.”  Dean nodded his head eagerly, letting his mouth open around Andrew’s thumb as he took in several loud, panting breaths, then closed his mouth around the digit again and sucked, rolling his tongue around it urgently.

“Oh yeah, you’re a needy one, aren’t you?  You need my cock in your sweet mouth?”  Andrew slid his tongue out and ran it over Dean’s lips, pushing at them as he went, feeling the give and cushion of Dean’s full pout.

“Please…” Dean panted.

Andrew smiled.  “Okay, baby.”  He brought his hand back and using both hands, shoved his pants and boxers down to hang roughly over his thighs.  His cock slapped up when freed than stood straight and hard in front of him as Andrew brought one hand to wrap around it at the base.  He let the other hand rest on one hip and leaned back, gazing down at Dean.  Dean let his eyes fly up to Andrew’s, then drop back down to his cock, a couple of times in a row.  He ground the hand that was on his own crotch down hard and then squeezed and twisted his hand repeatedly.  Then he did one quick swipe of his lips with his tongue and a hard swallow, then let his mouth drop open again, breathing his hot breath onto the hard cock that was just a fraction of an inch away.

Andrew nodded down at Dean and said lowly, “Go ahead, baby.”

Dean dropped his eyes to focus on the head of Andrew’s cock.  He was an average length, not tiny but nothing that would be hard to deep throat.  His cock was cut, but the head one of those small narrow ones that taper smoothly up to meet the size of the shaft.  A drip of precum was hanging from Andrew’s slit and Dean let his tongue slide out and lick it off in a slow, dramatic swipe, then slide back into his mouth.  He closed his eyes for two full heartbeats then opened them and leaned forward to quickly wrap his lips around the head of Andrew’s cock.  Andrew moaned softly.  From there Dean was in his element.  He let his mouth do the work, being sure to draw it out and take his time.  The blowjob was all this client was getting so he needed to make sure it was not just good, but amazing.  He worked Andrew’s cock and let himself enjoy it, too, rubbing and squeezing himself throughout.  When it was clear that Andrew was so worked up that he couldn’t string it out for too much longer, Dean let his noises grow, making muffled, hungry sounds as he fucked the man’s dick fast and rough with his own mouth.  He drew off occasionally, panting and swallowing to show his exertion at working over such an impressive cock. 

When Andrew started mumbling under his breath, Dean knew it was time. 

“Fuck…yeah…baby…you like that cock…don’t you…gonna make me cum…make me cum so hard…you want me to come, baby?  Yeah, you want to feel my cum…oh shit…” 

Dean rocked back and forth on Andrew’s cock, sucking hard, his cheeks pulled in tight and his tongue sliding over the veins and ridges underneath to the frenulum.  He sucked and slid and let a bit of drool slip out one corner of his mouth. 

“Oh god…fuckin’ yeah, baby…that’s right…oh fuck I’m gonna come for you, baby…”

Dean shoved his face hard against Andrew, his nose buried in the man’s pubic hair, the head of Andrew’s cock buried in his throat.  He swallowed hard around it and Andrew groaned loudly and suddenly tugged his head back hard by the hair.  Andrew’s other hand flew forward and wrapped around his cock and he started jerking it hard, holding Dean’s head back at a rough, almost painful angle.  He could see Cas, blurrily, but there in the background, still leaning against the wall, but staring at Dean with those intense blue eyes.  Dean squeezed his own cock and left his mouth open wide, tongue hanging out, panting roughly, this time for real.  Andrew’s come splashed onto his face, one…two…three spurts and then Andrew’s hand squeezed out the last couple small bits onto the carpet and let his head drop back and closed his eyes.  He still had Dean’s hair tight in his grip, so Dean didn’t move, just closed his mouth and licked his lips, squeezing hard at the base of his cock to calm himself.

After maybe half a minute, Andrew looked back down at Dean again and let go of his hair.  He brought a finger around and swiped it across Dean’s cheek, looking at the jizz on his finger for a second then feeding the finger to Dean, who swirled his tongue around it and then sucked, cleaning it off neatly.  Andrew fed Dean the rest of his come, then stepped back, slowly reaching to pull up his pants again, still staring at Dean’s face.  He put himself together, reached down to pick up his suit jacket and put it on.  Then he cupped Dean’s face with one hand and said, “Would you like to do that again sometime, baby?”

Dean nodded slowly and then watched as Andrew turned to nod at Castiel and then stride out of the room.


	3. Chapter 3

They were back in front of another door for Dean’s second appointment of the day.  Castiel was looking at him with those blue eyes that always made Dean feel like he was significant—to be seen and looked at so intently by a man like Cas—it still sent little electric jolts down his spine sometimes.

“So what are you trying to do for this client?”

“Make her feel confident...brave.”

“Good.  But don’t get too locked in to your thinking.  Remember to pay attention and follow her lead so you’ll notice if there are signs she’s after something else.”

Dean nodded.

“Are you ready, then?”

“Yes, sir.”

Castiel smiled and turned away, leading the way in.  

* * *

A few hours later, Dean was standing with Castiel in front of a similar door for the third time that day.  Castiel had refused to discuss the first two appointments with him until tomorrow. But Dean thought both of his first appointments had gone well.  He was sure that his second client, a somewhat overweight and shy, but very attentive and sweet woman, had left with a sense of safety and competence, ready to explore on her husband’s body what she had learned from Dean.

The third client was more of a mystery.  All Dean knew was that this client wanted to fuck him from behind and finish inside of Dean.  What mood or other preliminaries he might prefer, Dean had no idea. Despite his training, Dean was left a little nervous and it was clear to him that Castiel felt it was a valuable experience for Dean to go through.

Castiel led him through the door and shook Mr. Henricksen’s hand, giving him the usual spiel about Dean’s training and his presence in the room.  The client nodded absently, his full attention on Dean right away. He was a strong-looking black man with a shaved head. He wore a simple suit that fit well, showing off his broad shoulders and solid chest.  He stared at Dean intently the moment Dean stepped up beside Castiel. As Castiel stepped back and faded into the background, Henricksen stepped slowly around Dean, looking him up and down. His dark eyes were heavy, and something about them bothered Dean.  He shook it off and adopted his best attempt at a respectful, demure pose, his hands clasped behind his back, his head held straight, but his eyes slightly downcast. When Henricksen stepped back in front of him, he was still and said nothing. After a minute, Dean looked up.  The client was still staring at him. His face showed no emotion whatsoever. Dean smiled softly, just a little, and raised his hands, planning to reach out for the client’s tie, but Henricksen stepped back immediately.

“Not yet.”  His voice was low and assertive.  “I want to see you first.” He stepped back and sat down on the bed.  “Take off your clothes. Slowly.”

So Dean stripped.  It wasn’t a striptease—he didn’t sway his hips or turn around, he didn’t bat his eyes or lick his lips.  But he slid each piece of clothing off at a snail’s pace, with smooth, athletic movement, making certain that none of his movements would distract the attention from simply looking at his skin, his tanned and toned body.  The man’s gaze was like cold steel on him, and Dean couldn’t work up the arousal that he usually got from attention like this. Even though he was insecure, somehow he was also vain, and he was proud of how hard he had worked to look good and how pretty most people found him.  It made him hot to feel the penetrating eyes of another person’s desire sliding over his body. But this client—he showed no sign of desire. He was focused, but it was more like a laser than like the fiery glances Dean was used to.

When Dean was naked, Henricksen beckoned him closer.  When Dean was standing before him, Henricksen slid his hands up the sides of Dean’s thighs, rubbing his hands over Dean’s hips, then around behind Dean to cup his ass.  His grip grew tighter until he was squeezing Dean’s cheeks painfully. Dean looked down at the man, but he wasn’t looking at Dean—at least not at his face. His gaze was straight forward, apparently focused on Dean’s cock.  In Dean’s discomfort, he had not grown hard, and Dean was afraid Henricksen would be disappointed in him. He chewed his bottom lip uneasily, trying to figure out what this man wanted him to be or do.

Suddenly, Henricksen was pulling Dean roughly forward and pressing him down until he was laid over the other man’s legs, his ass in the air, one arm gripping the bed for leverage.  Henricksen’s left hand pressed down on Dean’s back, holding him in place, and his right hand was stroking over Dean’s ass in a rough, circular motion. Dean’s cock twitched between Henricksen’s legs.  He loved to be spanked. And he knew just what to do. He bowed his head down and let his right hand slide onto Henricksen’s ankle as he released a soft, sweet little whimper. Henricksen’s hand clenched his ass, then went back into motion.

Dean’s body started to rock forward and back, just the slightest bit, anxious and ready to feel that first strike.

“Dean,” he heard Castiel say.  His tone was patient but with a slight warning.

Dean turned his head to find Castiel, still standing across the room against the wall, but not leaning—standing straight with direct focus on Dean.  “Sir?”

“Remember the rules for today, Dean.”  Castiel’s voice was calm, not casual, but not angry.  Rules. Rules. Dean had no rules for today. He was there to serve his clients.  The client…had rules.

Dean stopped rocking and stiffened in Henricksen’s lap.  Henricksen had looked up at Castiel, too, and his hand no longer moved over Dean’s ass.  Dean slid out from under the hand on his back, ending up on his knees in front of Henricksen.  

“I’m sorry, sir,” Dean said, trying to adopt a similar tone to Castiel’s—something soft and nonaggressive, but still firm.  “I can only participate in the activities which were prearranged.” Henricksen was looking down at him with no expression whatsoever.  Dean sensed nothing whatsoever from this client, and was afraid flirting would not go over well, but without any other hints, he found himself slipping into that tone.  “But if you would be interested in coming back another day, I would love to feel your firm hand spanking my ass until it’s red and sore.”

Henricksen simply stared at him.  Seconds passed and Dean wondered if he should reach out—perhaps slide his hands up the man’s thighs, lean up and try to kiss him?  But the man was a closed book. Throughout the entire length of his training, Dean had never felt so out of his depth. What did this man want from him?  Why couldn’t he tell? Was he just a terrible bed partner? Was he going to fail and be sent away to a labor camp after all? 

Just as Dean was starting to feel tears start to will up in his eyes, Henricksen stood abruptly and said,  “Very well.” He started to strip, making quick work of his clothes, tossing them over Dean’s head onto the couch.  “On the bed,” he said to Dean brusquely, as he unbuckled his belt. Dean scrambled to obey, relieved to have an instruction, something to do to satisfy his client.  He settled on his hands and elbows, lifting his ass in the air and looking back over his shoulders to see Henricksen tug off his socks and step up to the bed.

“Are you prepped?” the client said, his tone still seeming cold and flat to Dean, even as he wrapped a hand around his cock and started working himself to hardness.  Dean’s eyes tracked Henricksen’s hand, watching as he quickly swelled to a not unimpressive size.

“Not yet, sir,” Dean said, wondering if that had been a mistake.  No preference had been stated by the client, and Castiel had given Dean the option.  Without anything to go on, he hadn’t wanted to prep too much or risk offending the client in some way by showing up with a plug already stuffing his ass, perhaps stretching him out more than the client would have desired.

“Do it.” Henricksen said, his hand slowing to long, lazy strokes now that he was fully hard.

Dean reached up to the bedside table for the lube bottle waiting there, slicking up three fingers, then reached back, his eyes on Henricksen, as he circled and rubbed at the rim of his hole.  For the first time he thought he saw a spark of something in his client’s eyes. He slid a finger in, smooth and unstopping, all the way, then immediately starting circling it inside himself, combining it with a partial in and out motion.  Henrickson’s eyes tracked every move and Dean waited only seconds before sliding a second finger in, then working himself open. The client’s gaze felt hot, and Dean finally thought the man must want him, but still he didn’t say anything or reach out to touch Dean in any way, leaving Dean still feeling uncertain.

When Dean pulled out and was about to slide all three fingers in, Henricksen’s hand was suddenly on his wrist, holding him back.  “That’s enough. I like it tight.” Dean nodded and tried to look aroused, but was sure he just seemed awkward and inexperienced.

Henricksen knelt on the bed, moving up behind Dean, and reached out to grab his hips, tugging him where he wanted.  Dean leaned forward on his elbows and let out a sort of whining moan as Henricksen lined up and pushed in. He was prepped enough—at least enough for Dean.  He usually loved a bit of painful stretch. But this client’s coldness and his own insecurities were starting to get the better of him, and he found himself wishing it were over already, even as Henricksen was still sliding in.  Where his training had finally begun to make him feel strong and powerful, able to coax any desired response from any client, he was now learning that he was still a novice. He knew nothing. How could he be expected to serve his clients when he couldn’t even tell what they wanted?

Henricksen was finally buried inside of him, and Dean felt the man’s fingers digging into his hips, pulling Dean back hard and tight against his pelvis as he rocked his hips in a circular motion.  Then he pulled out and slammed back in hard and started to fuck Dean in earnest, setting up a brutal rhythm that usually would have had Dean moaning and panting both for the client’s benefit and expressing his own pleasure.  But this client…he didn’t seem to want to hear anything from Dean. Instead, Dean buried his face in the pillow as Henricksen pounded away at his hole. The man made almost no noise, but he must have been feeling good, as his cock was harder than a diamond as it bore into Dean’s body.  Dean felt raw and used, another sensation he usually loved, but struggled to enjoy now. He closed his eyes and tried to imagine it was Castiel ramming into him with those powerful strokes, taking him, making Dean his. But it was impossible to fool himself. Castiel had used him in every conceivable way, but even fucking Dean this hard, he was so different than this man.  Castiel was never silent. And his fingers never felt so cold and cruel. And he rarely kept up any single rhythm for long—he would pause, change, move, touch, comment, caress, begin again.

Henricksen’s cock shoved in and out of Dean’s ass.  Endlessly. Over and over. Dean bit into the pillow and wondered how much longer.  The quiet in the room, other than Henricksen’s skin smacking into his ass, was unbearable.

Castiel was watching.  He was watching Dean, huddled on his hands and knees, just taking this fucking like a passive, shitty little househusband.  Not an experienced, trained, perfect little bed partner. He knew his mentor must be so disappointed in him. But he still had no idea how to do better.  Henricksen had given no sign that he would enjoy hearing Dean. And no sign what he would want to hear—would he like to hear a soft, pained whimper, making it clear he was big and Dean felt the stretch?  Grunts with every thrust, revealing the power of the impact and showing what a strong top he was? Moans of ‘yes’ and ‘more’ and ‘harder, please’? If Dean chose wrong, it would likely be worse than this simple silence.

Dean drifted as the other man used his ass, afraid to turn his head and see Castiel watching—afraid he would see displeasure in those perfect blue eyes.  He had utterly lost track of time and the moment when he realized Henricksen’s rhythm was stuttering and that somehow, unbelievably, his fingers had dug into Dean’s hips even harder.  A few more thrusts and the man was suddenly still inside of him, shouting out loudly, “YEAH, TAKE IT, WHORE!” as he pulsed and came inside of Dean. Dean’s knees shook, but he held still, feeling the warmth spreading inside his ass even as Henricksen pulled out and spread Dean’s cheeks, presumably watching some of his cum trickle out, then slid back in, giving a few more week thrusts as he came down from his orgasm.

Dean suddenly realized he wasn’t even hard.  He couldn’t remember the last time he hadn’t gotten hard with something or someone fucking his ass.  He felt his cheeks redden with shame. How could he have done so badly? Surely he would be given another chance—this was still a learning process, wasn’t it?

When Henricksen pulled out and released him, sitting back for only a moment before rising and reaching for his clothes, Dean pulled himself to a sitting position.  He had no idea what to say or do. And Henricksen seemed utterly uninterested. Dean slid over to the edge of the bed just in case, but Henricksen left the room without a word or glance to either Dean or Castiel as soon as he was dressed.

Dean hung his head, afraid of what Castiel would say.  A moment later, he felt Castiel’s palm on his neck and heard his low, warm voice say, “Let’s get you cleaned up.  You will sleep in my bed tonight.”

Dean’s heart swelled even as he fretted over the lack of reassurance in Castiel’s words.  Castiel had already told him they would discuss everything the next day. He could wait. As long as he would be near Castiel.  Maybe Castiel would even let Dean touch him. Or even make Castiel come. Dean loved the look on Castiel’s face when he came—he had memorized everything about it.  The way Castiel’s full, lined lips went slack and dropped open a bit. The way Castiel’s eyelids closed halfway and his brows pinched together. The way his chin lifted up and forward, exposing the line of his neck.

Dean stood and followed Castiel from the room, not even bothering to gather his clothes.

**Notes for the Chapter:**

> Thanks to the charming Fandorica for beta-reading this chapter!


End file.
